Acetone → 1-(3-methyl-4-aminobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole

HRID 2243245Notes

Reaction equation

HRID 2243245 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O)[CH2:5][N:6]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:8]([C:15]([F:18])([F:17])[F:16])=[N:7]1.C([O-])(=O)C.[NH4+].CC(C)=O>[Cl-].[Cl-].[Cl-].[Ti+3].O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[NH2:22])[CH2:5][N:6]1[C:10]([C:11]([F:12])([F:13])[F:14])=[CH:9][C:8]([C:15]([F:18])([F:17])[F:16])=[N:7]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 517165Ammonium AcetateHCID 592104091-(3-methyl-4-nitrobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole

Product 1

HCID 592103951-(3-methyl-4-aminobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazoleYield 92.9%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 1-(3-methyl-4-nitrobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole (1.4 g), ammonium acetate (30.5 g), acetone (60 ml) and water (30 ml), 20% aqueous solution of titanium trichloride (27.5 g) was added at room temperature and the mixture was stirred at room temperature for 12 hours. After finishing the reaction, the mixture was extracted with ethyl acetate, washed with saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate. After distilling off the solvent, the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-aminobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole (1.19 g).

Workup

  1. additionwas added at room temperature
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated aqueous solution of sodium chloride
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e8c2ea53ad5a4e639ed3a2cab7a2b6a7
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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